


Odd Looking

by Cach, littlebutter



Category: Teen Wolf (TV)
Genre: Blow Jobs, Come Eating, Crossdressing Stiles Stilinski, Cuddling & Snuggling, Cunnilingus, Dancing, Dating, F/M, Female Derek Hale, Female Ejaculation, Misunderstandings, Squirting, club
Language: English
Status: Completed
Published: 2014-03-02
Updated: 2014-05-29
Packaged: 2018-01-14 08:51:19
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 8,211
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1260334
Author URL: https://archiveofourown.org/users/Cach/pseuds/Cach, https://archiveofourown.org/users/littlebutter/pseuds/littlebutter
Summary: <blockquote class="userstuff">
              <p>Female!Derek and Crossdressing!Stiles meet in a club and fall in love.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> Derek = Derina (Der-ee-nah) I just liked it. :)
> 
> In the story Stiles is straight, he just likes to dress in women's clothing all the time but can't. :(
> 
> Um, yup. Hope you like the story. Please leave comments and kudos. :D

He is absolutely stunning.

Pale porcelain skin, legs for days, dark beauty marks that were waiting to be traced with Derina's tongue and he’s just dancing.

He's wearing a tight, black crop top with long sleeves and an equally tight, white skirt that cuts off above the knee with black at the waistband and stripe of it on the side. His shoes are black suede, ankle strap wedges and he isn’t wearing any jewelry except a plain, gold moon collar necklace. The make up he's wearing bring out his eyes and cheekbones perfectly and his lips are a dark plum color that goes so well with his fair skin. His wig is long, a warm rich brown, and wavy, like beach hair.

Fuck, Derina just want him. She wants to get her hands, mouth, and tongue all over his body. And what is more confusing to Derina than just wanting a man, since she’s never wanted one before, is the sheer amount of want. This seemed unfathomable. When she looks at him, she sees cemetery screening B-rated movie dates, and holding hands walking through the woods she grew up in, and making love, and lazy Sundays around her apartment, and just —just everything.

So, she’s determined to get him.

There are guys trying and failing to dance with him. It’s like he’s in his own little world, bobbing and flowing with the music. Maybe he’s straight and that’s why he’s ignoring them? Maybe he wants to get asked? Maybe he wants to just be alone? Fuck it, Derina’s going to go ask.

She starts to make her way past the other drunk people from her place on the wall. It’s hot and sweaty with everyone there dancing, but it is so worth it. When she reaches him, his back is to her and she has to tap on his shoulder. He turns around, stops dancing and his eyes get impossible wide. Derina just smiles, he looks adorable like that.

She closes the gap between them and says, “Can I dance with you?”

For a minute he just stands there, but then he nods his head and puts his arms over Derina’s shoulders and starts moving. Derina puts her hands on the thin strip of skin between his top and skirt and starts to move with the man.

“I’m Stiles."

* * *

 "I'm Stiles."

Holy fucking shit. Stiles is positive this woman is the hottest woman who has ever walked the planet.

She's wearing a fitted forest green Henley and tight black jeans that make her ass look amazing. She's also in black leather pumps and only wearing mascara. Her hair is a midnight black but it looks natural; its just slightly wavy and she has straight cut bangs that taper into layered hair.

"Derina. You look gorgeous." Goddamn, that smile. And her eyes! Stiles could get lost in those things. And jeez just dancing with her is making him all hot and bothered.

Wait. What did she say? Gorgeous. Shit, shit, shit, don't blush! Distraction!

"I'll have you know, I prefer handsome."

"My mistake. You look handsome, Stiles." Damn, definitely blushing now.

He saw Derina when she walked in. Stiles thought it was love at first sight, but the only other time that happened Lydia stomped on his toes and stole his crayons in the third grade, then eventually became one of his best friends. So, maybe he should take this one slower, not declare to the whole club that she is his one and only.

The club. Shit, he shouldn't even be in here. He's only eighteen; she has to be in her early twenties. Derina can drink and most likely is going to some fancy college. He’s barely a high school graduate and is going to community college to stay close to home, to take care of his dad. She looks so cool, probably looks like that all the time and sure Stiles looks good tonight, but his usual constricting jeans and graphic tee are nothing in comparison to Derina.

But dammit, if their bodies don't fit like a glove. This has to be something, right? He thought it was love, then she asks him to dance and tells him he's gorgeous. When she touched his sides it felt like buzzing underneath his skin. Right, it definitely something. Maybe it's homemade pizza nights, reading each other's books, giving her foot massages while she criticize reality television or takes a bath, and sleepy morning breath kisses on weekdays...

He’s going to get her, he has to.

“Want to get a drink?” She finally asks him. 

* * *

“Want to get a drink?”

They're dancing for about half an hour and its just them. God, it’s fucking magical. Looking into the other’s eyes, hands roaming, flowing with the music. It’s hot in there with all the other bodies, but it’s so worth dancing with Stiles. When the song cuts out and it’s like everything falls, but they’re still holding on to each other, breathing heavily.

Derina afraid to fall back on old habits, the ones she has to pick up any random girl. But she doesn't want to do that with Stiles, this isn't about predator and prey tonight. She doesn't want a one night stand with him. She knows this sounds crazy and absolutely absurd, but she wants this this guy forever. No how or why, she just knows that’s what she wants.

“Uh, yeah. Sure.”

Stiles seems a little unsure at first but then shows her a shy smile and grabs her hand to intertwine their fingers. Derina grins at him. She brings his hand up to her face and kisses his knuckles before guiding them through the mass of people.

But when they get to the bar Stiles looks even more nervous than before. "Are you okay? Do you want water, instead?"

He gives her a quick nod, "that'll be good, thank you." He looks away and then after a moment looks back at her, "I can't drink. Well, I can. But I'm not suppose to." And does a complicated motion with his free hand. She gets it then.

"You're underage?" She let's go of his hand in shock. Shit. She was about to ask him on a date. Hopefully have sex with him in the near future and then a whole lot of more sex if she was right about the gut feeling she was having.

"No, no, no, just to drinking! Just to drinking! I assure you I am a 100% consulting adult on anything besides drinking, gamble in Vegas, buy a car or a house without a cosigner, and go to most clubs."

Derina looks at him straight in his eyes and asks him, "How old are you, Stiles?"

"Twenty." Lie.

"Okay, I’m only nineteen." She raises one of her eyebrows.

"I turned eighteen in the beginning of April." He mumbles, turning his face away from her and his eyes cast downward.

Okay. That isn't so bad, right?

He’s eighteen and she’s twenty-two. They’re both legal, and... this is fine.

Besides, this is the first person she’s really wanted in a long time. It’s been almost three years of living the single life.

Kate, her first real girlfriend and only one up to the day, said she wanted to marry Derina and start a family with her, only to break her heart two years later. They were already living in New York at the time. In some shitty apartment, because Kate wasn't going to the school, but still wanted to go with Derina. Apparently, Kate heard Derina was going to NYU their senior year and came from old money, so she got with Derina. After a year of being together, the two left for NY. Derina went to college and got a job, while Kate was fucking around with the neighbor, coming up with whatever excuse she could to getting out of getting a job. It took Derina eight months to notice Kate was just using her, and when she confronted her, Kate told her she right. Everything came out that night. And when Derina just couldn't take it anymore, she called her sister Laura to pick her up and she spent the rest of the night at her’s. When she got home the next day, around eleven in the morning, all of the Kate’s things were gone along with the 2,000 dollars kept in the safe for emergencies. On the bed was a note in Kate’s loopy handwriting that said how she had one last good fuck with Matt, the neighbor down the hall, in their bed and that they were going away and to not bother looking.

It had been a rough few years but with her family support and college career she was okay. The only thing that was 'wrong' with her now was the walls she put up at any attempt to get into a relationship and her string of one night stands. But until now, it didn't bother her like it did her family, she was fine with that lifestyle. Perfectly fine. Until now.

"Okay. Just don't lie to me anymore, 'kay?" She smiles at him when he blushes and nods.

* * *

 "Okay. Just don't lie to me anymore, 'kay?"

Oh, that goddamn smile is going to be the end of him.

"So, how old are you then, Derina? Uh, I mean if you don't mind me asking. You don't have to tell me. It’s totally fine if you don’t tell me.”

“It’s okay." Derina says through an absolutely adorable giggle. "I’m twenty-two.”

“Cool. Cool.”

While Derina orders a water for him and a rum and coke with a couple cherries for herself, Stiles looks around and sees that there are a lot of people staring at them. He wouldn't doubt they are odd looking but he can't seem to shake the possessive/jealous streak that rips through him. The one that makes Stiles wrap his arm around Derina's waist and splay his hand across her hip.

Stiles thinks it’s probably not the best idea he’s ever had, but then Derina grins shamelessly and leans into him. Fuck the butterflies! Stiles just wants to sweep Derina up and take her to his... Goddamn it. To his fucking childhood bedroom. Yeah, that’ll totally impress her. What is he doing?

"So, Stiles, I was going to ask for your number? Maybe a date too?"

Stunned silence.

"Holy shit. Yes, totally."


	2. Chapter 2

Naturally the first and second date go on without a hitch.

Stiles was splitting his time between thinking about the perfect outfit to wear and figuring out the best way to win Derina’s heart. He had thought a lot about the way she acted that night, flirting when she had known Stiles was a man, and the fact that it was indeed a gay club they went to, so she could have possible been there to pick up a woman. Stiles was having a conflict, but was pretty sure Derea had to at least be a little attracted to guys. Even so, if he needed to play up his feminine side to get her, he sure as hell was going to! Yes, going to dinner wearing his cross clothing make him extremely nervous. Without the lights, music, and people dancing that just don't care, he was going to be very exposed. Then again, if having strangers stare at him was the price to pay to be with her, he would go to college dressed like that everyday.

Meanwhile Derina was fighting off her sisters and brother. Her whole family knew something was up, what with her smiling -the tiny thing that it was- and constantly checking her phone. Other than the pressure of not fucking up this new developing relationship there wasn’t anything on her mind to worry about. She had picked out her outfit days before, knew that her hair was going to be down like always, and had been on so many blind dates set up by her family that she knew what to talk about. This was going to be a piece of pie, all she had to really worry about was keeping him interested in her.

Date #1 is at a five star restaurants an hour into the city and they are both dressed to the nines. Derina in a bodycon gunmetal colored dress, black suede platform peeps, and of course her only nice, clean, perfectly fitted leather jacket. Stiles wearing an off-white, beaded collar dress and a khaki, fitted trench coat, with pointed burgundy velvet ankle strap heels. His wig straightened and put in a neat bun.

That date was about getting to know each other. Stiles finding out that Derina did in fact go to a fancy university, but was now going to local school to get her masters. Derina finding out that Stiles is going to stay and go to the community college in Beacon Hills, something that she was reluctant to, but did anyways, tell Stiles she was worried about. Him going off to college far away, that is. They also find out that they are both active, Stiles in the school's track team and lacrosse team, and Derina working out every morning and playing basketball whenever she gets the chance.

It ends with them making out in Derina’s car after she drives Stiles home, the Sheriff coming out and interrupting them. It was still amazing for both parties involved.

The second date is way more them than the first. They go to a cute, little diner the next small town over and the dollar theater after that, hardly watching the old Western movie as they cuddled and made out the entire time.

Derina in a long, flowing black high-low skirt paired with a basic black cropped tee and weathered brown leather low ankle boots. But of course her leather jacket to complete the outfit. Stiles is dressed in dark black jeans with a plain, pale orange, sleeveless ponte top and black and white [pumps](http://lghttp.11470.nexcesscdn.net/8050DB/Magentolive/media/catalog/product/cache/1/image/600x860/9df78eab33525d08d6e5fb8d27136e95/z/z/zzc-872_5_.jpg) with a cute design of foxes on them.

So. The third date stood to be the best one yet, right?

* * *

Stiles's doesn't know if its just him or if Derina has always acted like a chauvinistic bastard. Doesn't know if its because she's just nervous about what tonight is for them or if she's been like this the whole time and he just hadn't been able to see past the hearts clouding his vision, but it is seriously pissing him off.

He knows what he looks like, he dresses himself for god’s sake, but he isn’t actually a woman. Not that that is any reason to be getting treated like some kind of rare and priceless piece of glass. He would never do this to her.

It started out with Derina coming to the front door and telling the sheriff that she would have him back in one piece -like he couldn't take care of himself?-, then she opens and closes the car door for him -really?

If that wasn't enough, when they get to the small restaurant for their date - a cute one in the middle of downtown of the biggest, closest city to them- Derina decided he couldn't pick or pull out his own chair. She also thinks he can't take off his own coat. Being polite is one thing, but this is another.

When the waiter finally leaved after what had to be the most exasperated specials menu Stiles has ever heard, he confronts Der.

"What's your problem tonight? Are you nervous, because I'm nervous as well but you don't see me handling you like some breakable object."

"What?" Its obvious from the face she's making that Der hasn't had the slightest clue about what she's been doing. And Stiles feels the anger lessen in him, but the insecurity rising. Is he just like one of the girls she's fucked around with? Is she even less interested because he's a guy?

"Derina, I may dress in women's clothing and put on makeup, but I don't need to be treated like one from the 1950's."

Derina looks like deer in headlights while Stiles watched her go through the date in her head. He can see when she realizes what she’s been doing as her eyes widen even more.

“Oh, fuck, Stiles. I’m sorry. I know you're a guy. Its just that I'm falling back into old habits and... I'm just nervous, Stiles."

Stiles can feel his heart sink at this statement. Falling back into old habits?

“It’s okay, Der. Just- stop, okay? This is going to be like any other night with us, just a little bit more. No big deal. Okay?”

He knows he shouldn’t tell her it’s okay, because it seriously is not. She’s acting like an asshole, which is making him feel inadequate. And as another result, it’s making him feel like this isn't going to go anywhere. Like the love of his life doesn't want the same thing as him.

Its a terrible feeling.

* * *

As the date moves forward, it gets better. Derina stops the act and they start to be their normal selves.

Stiles makes her laugh by sticking spoons to his nose and Derina glares at the couple clearly annoyed from all the noise they were making.

By the time they're having dessert, Stiles has long since forgotten the horrible feeling that worked its way into his gut.

* * *

Stiles is one lucky bastard. Somehow, god knows how, he's managed to finally put his hands all over the most beautiful woman he has ever seen. And he’s so lost in it, so completely and utterly gone until, of course, he starts to freak out.

They’re in her apartment and Stiles is pushing Derina into the wall next to the door. He’s kissing her, one hand on her waist and the other squeezing her ass. That’s when he feels her hands moving, slowly going up from his shoulders to the nape of his neck. He can feel her kissing the outline of his jaw and starting to suck on his neck, and that’s when she pulls at his hair. Or rather, his wig.

It’s a tactic he supposes she’s used before, trying to get more surface area to mark. But when she gives it a little tug, it moves. And that’s when Stiles freezes. He suddenly feels uncomfortable in his own skin. He doesn’t have low self esteem, Stiles knows he’s pretty good looking, but this girl called him ‘gorgeous’, not ‘handsome’ or ‘hot’ or even ‘good looking’. ‘Gorgeous.’ Which is something that most people call women. Not men.

He realizes again, that this beautiful woman is a lesbian, has been all her life, knew from an early age. And the only way he even remotely looks like a woman is with hair and make up. If the wig comes off, what will happen? He loses that femininity. And what will Derina think then? ‘Oh, shit. I’m really with a man. Ugh.’ Is that going to be her heartbreaking realization?

Fuck. Oh my god. What is he going to do? What would happen? What if they take off his wig? Take off one of the main contributing factors that make him look more womanly?

So Stiles stands there, frozen, internally breaking down. Basically too busy on his own thoughts to realize Derina giggling into his neck.

“Stiles? Do you want to take it off?”

“Wh- what?!”

“Your wig, idiot, why don’t we take it off? We don’t want to fuck it up."

“I... You- you want me to take it off?”

"Well, yeah. We can't ruin it."

“But. It’s- um, like- a major part of the outfit and, like-”

Derina giggles more, “Stiles, I was hoping to get you naked. A lot more of that outfit would have to come off if I succeeded.”

* * *

“Stiles, I was hoping to get you naked. A lot more of that outfit would have to come off if I succeeded.”

This beautiful boy is so silly. Thinking that she would make him wear his pretty wig to bed.

Without waiting for a reply, Derea starts taking the wig off. She sees Stiles closes his eyes, trying to remain calm and steady and when the wig off, she sees him opening his eyes slowly, like he’s afraid to see her reaction. She can tell it’s been hard for him to show his masculinity, especially tonight when she was acting nervous and doing all those stupid chauvinistic things. She had been so dumb, but now she had to make him understand that she wants him. Clothes and makeup and shoes couldn’t be less important.

“Please calm down, Stiles.”

* * *

“Please calm down, Stiles.”

She’s not even looking at him! What the fuck?! How could she ask him to do this?! She can’t tell him to calm down!

He was about to speak his mind when he realized she was scanning the room and looking for something. Then her eyes stop, gazing into the kitchen, and without saying anything she walks there. Stiles is just standing there, exactly where she left him and has absolutely no idea what she’s doing. It’s at that exact moment that she pulls a blender from the kitchen counter and puts the wig on top of it. She fashions the blender into a makeshift stand.

Well, Stiles was definitely not expecting that. Here he was, bracing himself for the imminent rejection, maybe a polite excuse from her. Trying not to hurt his feelings but doing it anyways or something like that for sure, but not this. This was, Stiles was pretty sure, one of the nicest gestures he’s ever gotten just before going to bed with someone.

* * *

When Derina's finally happy with the way the wig looks, she puts it back towards the wall and turns back to him. She swears she's never used the word ogling in her life, but Derina is completely ogling him from where she's standing. She knows he's getting under her skin. And while she knew, from the moment she saw Stiles in the club that she wanted to spend her life with him, its still scary as fuck to see the changes in her life already.

But he's making her see light, for the first time in three really long years, Stiles is opening her up. She laughs so much when she's with him and when she's not, yeah, she misses him like crazy but its with a smile on her face. Stiles is making Derina so happy, its sometimes exhausting and she loves every minute of it.

“You can definitely pull off whatever look you want. Long hair, short hair… everything seems to work on you. God, you could wear a fucking hotdog suit and you'd still look beautiful.”

That's when she makes her way back to him. Back to Stiles and starts to kissing him, this time grabbing his real hair. And while she's tried to put in a lot of effort and make herself not look like an asshole for the dates, this is when she does stop thinking. She turns to the much more important task of making out with Stiles and Derina is pretty sure by now that she's never going to get over kissing Stiles. Every time is like the first time and she likes everything about it, his lips, his tongue, the little noises he makes, the way he grabs her… everything!

She also thinks that, somehow, kissing Stiles is not so different from kissing a girl. She knows she shouldn't be thinking like that, but somehow she can't keep the comparison away. Stiles is... soft like a women. There, she said it. Happy now?

Its an ambivalent feeling she has going on that makes her feel relief and guilty all the same. She promised herself from the start that she would, in no way, compare Stiles to any of the girls she been with. She doesn't want to compare him with a girl at all. She's beyond that, beyond the whole thing about how he looks and knows perfectly well he is not a woman, no matter what he wears. But the fears and insecurities are still there, and she can't really help those, huh? So yeah, she allows herself that tiny little comparison because somehow, without realizing it, he's making things easier for her. She doesn't think she would be able to kiss Stiles as confidentially and comfortably if he had with a full grown beard.

* * *

Stiles would give himself a hive five if he could right now. He did it! He got the girl! He's not wearing his wig and Derina is still there, kissing him like there's no tomorrow. And to make things even more incredible, she actually told him he looked good without it. So yeah, maybe he was just freaking out for nothing, right? He tends to do that a lot so it wouldn't shock him at all that— wait, what the actual fuck?! Oh my God, there it is again! She's man handling him again, pushing him against the wall while she takes his jacket off and she's pinning him there, pushing her thighs between his legs and fucking grinding into him until he’s about to burst.

And he’s not saying that women can’t do this, can’t be in control but when is she going to let him take the lead!? First it was at the house, then at the restaurant, and now this? Stiles doesn’t want Derina to feel like he thinks that she can’t do anything, but he wants to do nice things for her. When can he take care a few things for her? Especially this, because this is important to him, he wants to make love to her and all this is doing is making him think she just wants a fuck against the foyer wall. Just a fuck against the foyer wall with another woman.

Is he- is he just not enough?

He doesn’t realize Derina has started to watch him.

“What’s wrong, baby?”

* * *

Derina feels Stiles freeze under her and when she turns her head up to him, he's got this look on his face, like he's about to cry. He looks so upset and she doesn’t know what happened.

“What’s wrong, baby?”

"I… I just really need to know. Like, right now." When he takes a deep breath and let's it out, Derina feels in warm on her face, "are you attracted to me? As a man? Like, I know you said I could pull off any look, and we're not in a disagreement there," Again, she can feel the humorless chuckle they're so close to each other. "But I am a man. I have manly part under this skirt, Der. A penis."

She knew he was going to ask eventually, but still the question shock her. She was at a crossroads. She could either say no, she wasn't attractive to him sexually, but Derina would be lying and she knows she would be. Because, yeah this is completely new for her, but it’s Stiles and how could she not like anything that was under his skirt. But at the same time, she's scared shitless. She could just be honest, tell him she's in fact attracted to him, but when they get down to actual penetrative sex... There is going to be some hesitation. There’s no doubt about it. She’s never done anything with a guy and she has no idea what she's doing. How will that make him feel? Will he be disappointed that she’s not up for going all the way tonight, like any other girl he’s been with would most likely be okay with? Either way she is going to be upsetting him... And she's trying to make this guy fall for her? How the hell is she going to accomplish that, huh?!

Well, here goes nothing...

“Stiles... I am 100% sexually attracted to you. I’m just... I’m- scared...”

“Of me!?” He looks so shocked, with his eyes wide open and his mouth hanging by the hinges, it kind of... Makes her laugh. Loudly.

"No, you idiot! Oh god, your face right now! I've just never been with a guy before! That's all." She says between fits of laughter. "I just want it- it to be good-" Great, now she has the hiccups. "for you-. And I'm- ugh- I don't think I'm- up for- going all the- the way tonight-. -I'm nervous-."

* * *

"-I'm nervous-."

Holy shit. Stiles didn’t even think about how this would be Der’s first time with a man. All this time he had been thinking about how he felt and not giving a damn how Derina felt at all. He’s been so selfish in thinking that his problems are the only ones right now. They need to talk this out.

“Der, I don’t think we thought this through. Like, I’m scared that you won’t like my junk-”

“I do like- your junk-!”

“I know that, now! But I’ve been freaking out about it for days! We need to talk about all this shit. We need to talk about how I would never do anything you aren’t comfortable with. We need to talk if you think that all I wanted tonight was to go all the way. Because that’s the furthest thing on my mind!”

At this Derina gives Stiles the most doubting face she could possibly muster and, yeah, Stiles should probably take that back.

Actually, no. He’s not going to talk that back.

“Yeah, that’s right, Derina. Because I don’t want to just get to third base with you. I don’t want to just stick my dick in your vagina. I want to make love with you Der. I want this night to be fucking magical and if that doesn’t include penetrative sex then so fucking be it!”

There's a horrible, stifling, pregnant pause and Derina looks like Stiles just overwhelmed her with all the info he shared. But he doesn't give a mad fuck. He said what he wanted and now the ball is in Derina's court. He just has a little hope that this blindsided look will pass quickly...

"Well?"

* * *

"Well?"

'Well' he says. Shit. Derina just guesses that the safest route to go will be the honest route. Bad thing being she sucks at this shit. Good thing being she doesn’t have hiccups anymore.

“I- I want that. I want to... make love...”


	3. Chapter 3

**Notes for the Chapter:**

> Thank you so much littlebutter for making me a part of this amazing story!! LUVYA <3

Kissing.

Kissing is the most easiest thing to do with someone you love.

It can be simple and sweet or messy and fast paced. When you're sad after an angsty movie or when you're happy covered in mud because you guys decided to wrestle in the back yard after the flash flood passed.

But it is always easy. Just like now.

Because now it meant Stiles and Derina were kissing and kissing was easy for them. Like both of them had hoped. They loved each other, it didn't matter that it was so early in their relationship. They both knew the other was the one for them.

“I love you.” Stiles whispers in Derina’ ear as they move to the mattress.

It makes Derina pause as she starts to lower herself after taking off her final piece of clothing. Her heart is beating even faster than it was a minute ago and still the only thing she wants to say rolls of her tongue like it wouldn't have stopped if she tried. Not that she would want to try. "I love you too."

Stiles giggles as Derina drags his mouth to hers.

"Thank fucking god. Because I love you so much and I know it's early, but I do. Der, I just love you. I love you—."

"Stiles. Shut up and kiss me."

Derina brings Stiles once again to her mouth and starts to hike up his skirt to pull off his panties. But then she feels his dick smack her right between the legs. Hitting her on the slit of her wet pussy and making her gasp.

"Stiles." She moans, "like that please, just like that."

She feels Stiles teasing her clit with the tip of his hard dick smearing his precum into her folds and mixing it with her own slick. From their talk earlier she knows he won't thrust into her and she's grateful that he'll be respectful of it. He doesn't even seem to be put out by the restriction and that makes her leak even more into his dick. He's loving this closeness as much as she is.

Her pussy is soaked as he grinds his cock between her folds making them both even more sloppy from all the fluid steadily dripping from her hole.

"Stiles... Please... You feel so good.”

And just like that, all at once, the weight of his body on top of hers is gone. Derina's eyes fly open, scared and panicked because the physical connection is completely gone and she's afraid she fucked up. But as soon as she sees him, she hears him.

"Ugh! Get this stupid skirt off me! Der, help me! The zipper busted and it keeps pinching my ass!"

As all her fear settles at once she can´t help but laugh a second time tonight because of her lover.

"Seriously, baby?!"

* * *

"Seriously, baby?!"

"Stop laughing, Der! That stupid thing was hurting me! I will get you back, dickhead."

Derina yelps as he jumps back onto her and Stiles can't help but grin, affection and arousal coloring his face. He kisses her once on the mouth, a quick peck before he descends down her body. Kissing her jaw, then neck, and sucking little marks on her collarbone and shoulders. He pays special attention to her nipples, they're hard and just a few shades darker than her skin but not only that, they're huge. Her areolas are at least the diameter of the top of a soda can and her nipples are stubby. He's never been with a girl who's had as big of nipples, but they're turning him on more than he thought they would. They're gorgeous and smooth and all he wants to do is suck on them all day, make them red and raw, but he can’t right now. He's on a mission, not to just tease Derina but to make her scream and squirt as he brings her to the best orgasm of her life.

He's going to make damn sure of it.

He gets his head down between Derina’s legs she’s already shaking and writhing under him. She’s begging Stiles to let her cum and he can honestly say it’s the most sexiest, most beautiful thing he's ever seen.

He licks Derina's clit in one long wet sweep and then goes for it. Sucking her clit into his mouth and flicking his tongue back and forth over it. He can't begin to describe the taste of Derina as he dips between her fat, hairless lips to drink up her fluids.

"God, Der. So good, you taste so good, Der."

As he suckles her hole as his thumbs hold the blood engorged folds open and with his index finger he teases the nub of her clit. He inserts a finger when she pushed her hips into his face and goes straight to her g-spot. He wants to make her squirt but he's realistic. She might have had a lot of one night stands but squirt takes practice and it might take a few times if Derina's never done it before.

She's moaning and gasping and pulling his hair. Cursing and saying his name like a prayer and Stiles fucking loves it. She's so soft and hot, like what he would hope new pahoehoe lava felt like.

"Oh my god, Der. Fuck— I wanna make you cum.”

Stiles adds another finger and starts to climb back up Derina’s body, still moving his fingers inside her. He kisses her neck, sucking little red spots that her shirts won’t cover up and whispers in her ear, “I’m gonna make you come so hard, you’ll never forget it. You’ll never want anyone else, but me. Only me, Der.”

Stiles feels Derina’s g-spot swelling and he knows he’s going to have to calm her. He’s never felt what it’s like to squirt himself, or have had the pleasure of making someone else squirt, but with all the research he’s done on the subject he knows she’ll feel like she has to take a piss.

She starts to squirm and he has to bring his body down again from where they were making out in order to stop her from crossing her legs. She’s whining now, moaning that it’s too much.

“Stop, Stiles. Stop. Feels like I’m gonna pee.”

“It’s okay, Der. It’s okay, just let go. It’s going to be so hot when you squirt all over me. You’re going to cover me in cum, I know it. You’re going to be so amazing at this. Trust me.”

Stiles can feel when she finally relaxes and trusts that she wouldn't piss on him or even if she does he wouldn't get mad or disgusted by it. Her legs stop squeezing his ribs trying to make him stop, her hands go lax in his hair as opposed to pulling on it and her head sinks back into the pillow. She's all his for the taking.

"Thank you, Der. Thank you so much. You're going to love this."

He lowers himself even more and starts to suck on her clitoris again. He's moving his fingers inside Derina again as well and making them curve up and press on that filling gland. He uses his other hand to pet her stomach, trying to make her even more reassured.

When she starts to continuously spasms from the onslaught of sensations to her cunt, he presses the hand on her stomach over the pelvic bone and brings his mouth off of her clit.

"Come on, Der. Cum for me. Please. I wanna taste you. I want your hot juices all over my face and chest. I want—"

She screams so loud when she cums the second thought that runs through Stiles's head after, 'holy fucking shit! Yes!' is 'I hope no one calls the cops.' But then he can think of anything as he's mouthing at Derina's soaking wet pussy. Its all over her thighs and some making a path to her ankles. It's covering his face and dripping from his hair. And the taste. It's not the most pleasant thing you can think of but it's all Der. His Der. Its musky, a little sweet and just makes him want to eat her out more. Suck every last drop from her raw cunt.

When he manages to pick his head up from between her legs he sees Derina still shaking and some tears flowing from her eyes. He wipes his hand down his face and pulls up to kiss the tears away.

"Der, you okay?"

* * *

 

"Der, you okay?"

Derina could barely open her eyes after she came. Her body was still shaking. She tried to shield herself away from Stiles as he was licking up milky liquid that shot from her body, he was so engrossed with getting every drop from her swollen pussy that she couldn't get his attention.

She nodded to him, "I'm 'kay."

"Good, because I still need to clean you up."

She moans again when he slides down and teasing licks her clit. But he doesn't stay there. He slides over to her ankle and mouths at it. She can feel him following the trail of cum she covered herself it and she relaxes under his perfect touch. He knows not to mess with her cunt right away.

When he gets to the inside of her thighs she´s ready to go again but she knows he hasn't cum yet. She's been getting glances of his still rock hard cock bouncing in between his legs. She places a hand on his head before he gets to her entrance.

"Stop. Stiles, I wanna— Stiles, I want—"

"What, Der? Whatever you want."

Derina has a feeling that he thinks she wants Stiles to fuck her. And Derina can't, it's still too new for her and he's going to give her a little while to get comfortable with the new appendage that is being introduced into her bedroom. But that's not to say she doesn't want to taste, want to feel, want to make him cum from her mouth alone.

"You're gonna cum in my mouth."

Derina doesn't wait for a reply as she sits up and gets up on her knees facing him. She knows the basics of how to give a blowjob from Laura's over sharing of her summer flings. That doesn't mean she's going to be any good at it. But when in doubt, fake it till you make it.

She steadies him with one hand holding tight on his hip and the other grabbing his fat dick and bringing it to her lips. Sucking the tip into her mouth and guiding her hand down from the length to his balls, fondling them.

As she sucks down his length trying to get more in, Derina can't help herself as she guides the hand around Stiles's balls even lower, teasing his puckering little hole. The loud moan and tugging on her hair encourages her to do it even more. She knows Stiles is fucking loving this and so is she but when she can't get enough in her mouth she growls. It's tougher than she thought it would be and her big mouth isn't doing much to help as one might think. She just can't get his cock all the way in like she wants.

So focused on trying to get her beautiful boy off she doesn't see the little smirk on his face as he gasped and moaned through his grinding teeth. She did feel it though, when his sticky, cum covered fingers slid back into her still tight cunt. It's too much but she can't help but fuck herself back on those long fingers.

She pulls off his cock to catch her breath and moans, "holy fuck, Stiles. Please. Oh, god, yes..." Moaning again as she feeds the spit covered dick back into her mouth.

Its when she starts to slide the tip of his cock over her back molars that Stiles finally cums. She looks up just in time to see him throw his head back, tighten the hand in her hair and pulls his fingers out of her wet cunt to thrust one into the twitching pucker of her asshole. And the pain pleasure that hits her is enough to have her cuming again.  
They fall to the bed after the initial shock fades faded, curling around each other at the foot of the bed not bothering with blankets as they drift to sleep.

* * *

 

Derina gets up the next morning at five to make her daily fruit smoothie and go for a shorter jog than normal around to the Italian bakery. She figure she can get him a cup of coffee and they can share a few pastries before he has to get back home.

What she absolutely doesn't expect is to come home to an apartment that smells sweet of breakfast foods. The small bar that connects the living room to the kitchen is filled with plates of panqueques with dulce de leche, tortas fritas, and some mugs filled with yerba mate.

There is just so much food and Stiles is still in the kitchen cooking up a storm. The oven and all burners on the stove are on.

"Baby?"

"Ah! Holy shit, Der." He laughs as he turns around, flour powdering spots on his face, "You're back! I saw the blender in the sink so I figured you went out on a run. I made breakfast for you. Hope that okay."

"Yeah, of course. I don't think you need to make any more though, baby, its only us two."

As they eat Stiles explains that one day he was surfing the web to try and find recipes that would enable his sweetened condensed milk obsession. He dug through the Argentinian tab in the 'around the world' section on a food website and found what he made today. Apparently those ingredients were the only things in the pantry and Derina needs to go major grocery shopping so her boyfriend can start to make her delicious food.

* * *

 

After the huge breakfast— where most got put in the fridge because neither one could consume that much food— they go lay on the pull out couch and watch some TV. Though, not too long after Derina's hands starts to wonder.

"You're such a cougar, Der." Stiles laughs, "taking advantage of my young, lean body."

"I am not, you jackass."

All Stiles can do is laugh some more.

"Yes, you are. You're just like a big, bad wolf. Inviting me in and taking my heart."

As he says this he rolls to his back looking up to Derina as she leans on her elbow. Stiles smiles at her with such admiration and devotion she knows that what he just said the truth.

She stole his heart and she's going to be damned if she ever let's go in the slightest.

"I'm not just a wolf then."

"Oh, yeah? What are you?"

"I'm the Alpha!"

And that's when she tackle him with kisses to his face and hands pulled up above his head.

* * *

 

Getting ready to go home is more difficult than Stiles originally thought it would be.

They talked a lot during the day. A lot about Stiles's crossdressing, a little about Derina´s insecurities, and almost the whole time about their future.

Derina wanted Stiles to meet her family and he wanted her to meet the Sheriff. Derina wanted Stiles to move in with her after a while, neither wanted to marry but both wanted kids later in life. Derina vetoed getting pregnant herself though, so they were both pretty sure adopting was the way to go.

Getting out of the shower Stiles is thinking about how he still doesn't want to leave. He goes to rummaging through the draw under the sink to find a pair of Derina's undies that would fit him when he spots her makeup bag. He looks back down, sees black lace and an idea starts to form.

He grabs the things he needs and gets to work.

* * *

 

Derina is on her phone when Stiles comes out of the bathroom. Its like in the movie Weird Science, when Kelly LeBrock walks out, fog rolling behind her and what damn will be the most sexiest thing to ever be seen.

But fuck, this is even better. Stiles, coming out of the bathroom, steam coming out around him, dressed in her own tight, black lace boyshorts and Dior lip stain, along with smokey eye make up. The dark colors against his pale skin make him almost glow. He looks powerful and confident, like he always is in make up. Derina thinks he especially loves wearing lipstick, always taking it off at the last second, always looking regretful.

He walks over to her as she lays there, propped up against the headboard. Derina was in the light blue lingerie that she knew Stiles's loved against her olive skin tone. He called her beautiful in them when he caught a glimpse one night making out.

"So that what took you so long?" She asked when Stiles gets to the foot of the bed. "Getting pretty for me, huh?"

The hungry grin Stiles gives her makes her break out in goosebumps.

"Always."

He slides on to the bed and pull her toward him by the waist, slowly taking the stupid blanket that's covering her legs. Once he has her under him he starts to nose at her cheeks and jaw, quickly avoiding her lips when she tries to kiss him. She moans in displeasure.

"Nuh ah, you have to wait."

Stiles starts to move on to her neck, lightly grazing her with his lips and ghosting her shoulders with his fingertips until he carefully places a kiss in the middle of her neck, sweet and chaste. Then he's moving down again only touching her with his nose, almost as if he was trying to smell every centimeter of her body, when again he stops, and places another kiss right on her heart. He continuous his journey and stops again for another kiss, right above her right ribs but this time he chuckles a little.

"What are you laughing at?" She pants as she gets on her forearms to look at her boyfriend. "What are you doing? Making a kissing path?"

"Uh huh." Is the only answer she gets, Stiles being too busy placing another kiss at the top of her belly in the same deep color of his lips.

"Afraid of getting lost, baby?" She giggles as he finds her only ticklish spot and kisses it.

"Maybe." Stiles tells her from his place between her legs and head on her stomach.

"I wanna make sure I'll always find my way back home." Moving further down for the final time, placing another stain of lipstick on her lower belly and above the mound of hair between her legs.

**Author's Note:**

> Disclaimer: I don't own the show, characters, etc. It would have been more porn, less plot if I did. (And Derek and Stiles would have done the deed in season one. ;))
> 
> PLEASE! If I messed up - spelling, grammar, incorrect/offensive terms - leave me comment. I will fix it as soon as possible and learn from my mistakes.


End file.
